


Wincest Love Week Fic Collection

by doilycoffin



Category: Supernatural
Genre: Crossdressing, Fluff, Implied/Referenced Underage Sex, M/M, Priest Kink, Truth Spells, Weecest, references to Dr. Sexy/Dean/Sam
Language: English
Status: Completed
Published: 2016-02-17
Updated: 2016-02-17
Packaged: 2018-05-21 04:45:17
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 8,348
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6038602
Author URL: https://archiveofourown.org/users/doilycoffin/pseuds/doilycoffin
Summary: <blockquote class="userstuff">
              <p>A collection of the fics that I submitted for Wincest Love Week. Each fic is self-contained and  correlates with a certain theme.</p>
            </blockquote>





	1. Things They Love About Each Other

**Author's Note:**

  * For [random_firework](https://archiveofourown.org/users/random_firework/gifts).



> These fics are dedicated to [random-fireworks](http://random-fireworks.tumblr.com), the lovely person that I was assigned to during the exchange.
> 
> Concrit is welcome.

**Summary for the Chapter:**

> Sam has a thing for the way Dean smells

He’s embarrassed to admit it because Dean would give him endless grief over it, but Sam can’t get enough of Dean’s smell. No matter how often Dean has switched aftershaves over the years, there’s still something underneath it that is uniquely Dean and makes Sam feel at home. When Sam first got to Stanford and suffered through those first unbearably lonely months, he would take a pilfered shirt of Dean’s that he packed into his bag on impulse and put it over his pillow at night so that he could bury his face into it and pretend that he was still sharing a motel bed with Dean (and if he jerked off a couple of times while doing sniffing his brother’s shirt, well, he never claimed to be a perfectly well adjusted person). 

These days, he and Dean aren’t apart for too long very often but every once in a while Dean will be away from the bunker for a couple of days and Sam will pine like the mopey teenage girl that Dean so often accuses him of being. When he’s especially desperate, he’ll even wash his hair with Dean’s 3-in-1 shampoo because it reminds Sam of him even though Sam doesn’t really like using something that claims to be shampoo, conditioner, AND body wash (he’s not half the priss that Dean says he is, but he makes an exception for hair care). 

When Dean gets home a few hours before dawn one morning after a fairly non-strenuous but prolonged hunt for an oddly discerning ghoul with a penchant for the flesh of middle-aged Italian men (Dean almost regrets killing it before he had the chance to ask what the hell was up with that), the only thing he wants to do after he gets out of the shower is go the hell to sleep. To his surprise, he finds that his bed is already very much occupied by a certain little brother who’s curled up on it and, upon closer inspection, wearing one of Dean’s oversized hoodies. Sleep doesn’t come doesn’t come easy to Sam these days (or to Dean for that matter), so rather than announce his arrival, Dean quietly strips down to his underwear, creeps towards the bed and gently spoons up behind Sam in the hopes that he won’t wake up. When he buries his face in Sam’s nape, he can tell by the familiar smell that Sam must have been using his shampoo while he was gone, and the deduced reason why makes him feel a strange combination of fondness and horniness. 

Dean is shaken from his reverie when Sam’s sleep-raspy voice, half muffled by a pillow mumbles, “I didn’t think you’d get back this early in this morning.” 

“Yeah, I finished up the hunt and didn’t feel like staying another night in a motel. I missed sleeping in my own bed.” The “I missed you” is left unspoken, but Dean figures that Sam is smart enough to read between the lines. “Sorry for waking you up. I tried to be quiet…figured that you’d get so excited by my highly anticipated arrival that you wouldn’t be able to get back to sleep if I woke you.”

“Actually,” Sam says in a marginally more awake voice, “ _your_ excitement was poking me in the back and woke me. Did those lonely nights on the road leave you hard-up, Dean?” 

It wasn’t until that moment that Dean realized that he had indeed been sporting an erection that was currently grinding against Sam. “Oops, sorry,” he apologized a bit sheepishly with a kiss to Sam’s shoulder, “but while you’re up, do you wanna help me out with this or do you want to tap out and leave me to a romantic encounter with my right hand?” 

Sam rolled over to face Dean. “Yeah, yeah,” he muttered with a yawn while his hand was already creeping towards the hem of Dean’s boxer-briefs, “c’mere.” 

Sleepy, slightly-uncoordinated handjobs definitely didn’t constitute as the most exciting sex that Dean and Sam ever had together, but they both came soon enough and it wasn’t long before Dean was right back where he started with his body plastered against Sam’s back, his thumbs rubbing idle circles on his hips. 

“Not that I’m complaining or anything,” Sam broke the easy silence, “but what brought that on?”

“You’re wearing my hoodie and you smell like my shampoo…did you miss your big brother, Sammy?” Dean asked teasingly. 

Instead of denying it like Dean half-expects, Sam easily admits “Yeah, I guess I did, just a little bit. That got you raring to go?”

Dean figures that he should reward Sam’s honest admission with one of his own. “I guess I like the idea of you missing me and using my stuff while I’m gone. It’s kind of nice to miss each other when it’s not because one of us has been kidnapped, murdered, or dumped into Hell. It feels like something that normal couples do.” 

Sam’s quiet snores make Dean think that maybe he didn’t catch all of that (and part of Dean is slightly relieved because his speech had been verging into, if not outright chick-flick territory, then at least chick-flick adjacent) and he soon follows his brother into a peaceful slumber.


	2. Hurt/Comfort

**Summary for the Chapter:**

> Dean gets sick and has a certain request for his brother

Sam never fails to be amazed by the fact that his brother will barely complain when he gets his arm ripped half-off by a wendigo and instead make a bunch of tacky jokes about how he’s glad that at least it wasn’t the arm he uses for jerking-off and yet a simple cold will turn him into the sulkiest human being on the planet. It’s a little strange, Sam thinks, because Dean was actually pretty stoic whenever he got sick as a kid and he’s pretty sure that Dean never complained back then because he was always so focused on caring for Sam and appearing strong for his little brother that he would have felt guilty if Sam worried about him being sick. The idea of this makes Sam feel both sad and a little bit fond because he’s glad that they’ve gotten to the point where Dean is okay with Sam taking care of him, even if it means showing weakness. And while Sam certainly doesn’t enjoy seeing Dean be miserable, he can’t deny that he relishes the rare chances he gets to take care of his brother and doesn’t mind indulging (most of) his whims.

Currently, said brother is laid-up in the bunker with a truly impressive mountain of used Kleenex on his nightstand. He’s quite a pathetic sight with his hair limp and messy, eyes bloodshot, nose bright red, and his face somehow pale and flushed at the same time and it awakens some weird, dormant maternal instinct in Sam that tells him to wrap Dean in a cocoon of blankets and pour soup down his throat until his cold is coddled into meek submission. In fact, Sam was bringing in a bowl of soup to Dean’s room to do just that when the sound of a raspy voice reaches his ears.

“Sammy,” Dean croaks, “can I ask you somethin’?”

Dean’s solemn tone immediately causes Sam’s brow to furrow in concern and he leans a little closer to Dean. “Of course, man.”

“It’s really important, Sam. My life may depend on it” Dean continues seriously, and the pit of anxiety in Sam’s stomach grows as he tries to figure out what Dean is about to ask him. Is Dean somehow much sicker than they both originally thought?

“Sam…will you please put on a nurse’s outfit and— wait Sam, where are you going?”

“You’re clearly delirious, so I’m gonna go grab the thermometer and make sure you don’t have some kind of brain melting fever brewing up,” Sam says dryly. “Furthermore, I don’t see the point of getting dolled up for you anyway. Even if I _had_ a nurse’s outfit lying around, you’re so sick and doped up on cold medicine that I doubt you could even get it up right now.”

Dean looks vaguely offended. “Aw come on Sammy, you know better than to underestimate my dick; Dean junior is a real trooper. Besides, it would make me feel better. I’m pretty sure that the sight of your ass in a sexy nurse’s outfit could bring me back from the brink of—“

Sam doesn’t get to be blessed with the rest of the shockingly coherent (he wasn’t kidding when he said that Dean was pretty doped up) rebuttal before Dean is overcome by a fit of coughing and hacking that has him rubbing Dean’s back reassuringly until it passes.

“I’ll tell you what: I won’t put on a nurse’s outfit,” and here he is interrupted by Dean grumbling before he continues, “…but I’ll stay in bed and cuddle with you and let you pretend in the morning that you didn’t let yourself be the little spoon.”

Dean apparently finds this satisfactory because he does just that. Later that night while he leans his head in the crook of Dean’s sweaty neck and listens to the reassuring but wheezed sound of his breathing, Sam thinks maybe when Dean is feeling a bit better in a few days that he’ll have to get his hands on a nurse’s outfit after all. Dean’s right: his ass really _would_ look amazing in it.


	3. Weecest

**Summary for the Chapter:**

> Sam (the kinky little minx) gets caught shoplifting and Dean has to bail him out of trouble

Sam considers himself to be a fairly well-adjusted sixteen year old boy, thank you very much. Well, aside from the fact that his family hunts honest-to-god monsters and all other things that go bump in the night. And, okay, the whole “fucking his brother” thing might also be working against him, so maybe “well-adjusted” is somewhat of a stretch, but he likes to think that he’s at least kind of normal-ish. And it’s perfectly normal and healthy for a teenage boy to explore different facets of his sexual preferences. In fact, he’s pretty sure that a lot of guys like wearing women’s clothing and fantasize about someone hiking up their skirt and fucking them while they get told what a pretty girl they are. Admittedly, there are probably a lot fewer guys out there who have to hide erections whenever their brother jokingly calls them “Samantha” but, again, Sam is only shooting for “normal-ish” here, so he firmly believes that he doesn’t have anything to be ashamed of.

Well, at least that’s more or less what Sam is going to tell Dean after he gets picked up from freakin’ mall jail for shoplifting a skirt after his brother inevitably gives him all kinds of crap for it because there’s about a 100% chance that Dean will see through his bullshit “it was for a dare” excuse that seemed to work on the mall cop. And yet, as well crafted as he believes his rationalization to be, it isn’t exactly making him feel better at the moment. It would probably help if he at least attempted to steal a classy, plain looking skirt instead of an obscenely short pink one. With lace. And ruffles. It’s not _his_ fault that the color looked good against his skin, dammit. It is, however, kind of his fault that he was so consumed with lust at the idea of showing the skirt off to Dean (if he ever actually worked up the courage to do it that is) that he was sloppy and managed to get caught red-handed while stealing the stupid thing. Yeah, Dean is never going to let him live this one down.

When Dean finally arrives, Sam is thankful that the news of him getting caught shoplifting a skirt for a “dare” is met with nothing more than a raised eyebrow from Dean and a sincere promise that his little brother really is a good kid, officer, and it’s just that moving around a lot makes it hard for him to make friends and he sometimes falls in with a bad crowd but he’ll never shoplift again, honestly. Somehow Dean’s charm in combination with Sam’s perfected ability to look sincerely apologetic allows him to get off with a warning. The car ride back to the motel is blessedly quiet and Sam foolishly begins to believe that Dean might really let this one go and silently agree to never speak of it again. These hopes are quickly dashed when Dean pulls up into the motel parking lot but makes no move to get out of the car and instead turns an expectant look at Sam.

“Alright Sammy, you wanna tell me why you _really_ tried to steal a skirt of all things?,” he asks.

Sam scrambles for a second before sputtering, “Uh…a dare? I’m a troubled youth, Dean.”

“Bullshit,” Dean snorts.

Damn it.

Sam sighs and realizes that the jig is up. He might as well just come clean now; if Dean makes fun of him for it until his dying day, then so be it.

“Okay fine. It just…looked nice. And sometimes I think about wearing stuff like that while we…you know,” he says while looking firmly at his feet.

Dean is quiet for so long that Sam starts to become genuinely concerned until he finally speaks up.

“You wanna look pretty for me, Sammy?,” he asks, and he doesn’t _sound_ like he’s mocking Sam. In fact, his voice sounds kind of wrecked and when Sam looks up and sees a definite bulge in his brother’s pants, he starts to think that maybe Dean is way more into the idea than he expected.

A mischievous grin works its way onto Sam’s face before he puts on his best seductive voice and says “I wanna look real pretty for you, Dean. I love thinking about getting all dressed up for you in some nice heels and a skirt; you wouldn’t even have to take it off before you fucked me and told me what a dirty girl I am. I might even wear a little makeup…I can’t even guess how long I’ve stood in lipstick aisles while trying to figure out which shade would look best on your dick after I blew you while wearing it.”

Dean lets out a strangled groan. “Jesus Christ Sam, you can’t just say things like that. Blood went rushing to my dick so fast that I’m pretty sure I almost blacked out.”

“Hey, you asked,” Sam says smugly.

“Yeah, yeah…I still can’t believe you got caught stealing, by the way. What are you, an amateur? I’m a little embarrassed for you, Sam.”

Sam’s smugness immediately turns to sullenness. “ _You’re_ embarrassed? I’m the one who got caught clutching the world’s girliest skirt in their hands before getting dragged out of the store by security. People laughed, Dean.”

“Hey, it could have been worse,” Dean says wryly, “at least you weren’t caught trying to shoplift panties or something.”

“Nah, I stole some of those ages ago…”

Dean scrambles to get out of the car so franticly that he manages to bang his head on the roof of the impala and nearly concuss himself before he all but drags Sam into the motel room.

Yeah, this misadventure is _definitely_ working in Sam’s favor.


	4. Curses

**Summary for the Chapter:**

> An ex-tryst of Dean's puts a...unique curse on him.

**Notes for the Chapter:**

> I would probably place this early on in the series around season one or two

It’s no secret that Dean has slept with a lot of women over the years while he enjoyed some much needed downtime after ganking whatever fugly monster was terrorizing the fair citizens of whichever town he landed in. He’s traveled all across the continental U.S. and behind him lies a trail of one night stands (and very satisfied ones at that). He likes sex, alright? Sue him. And, on rare occasions, he’ll bump into said one-night stands if another hunt happens to lead him back to that same town. Normally, this isn’t an issue; at worst, the encounter slightly awkward and at best, he manages to score a round two with the woman in question. After heading to a bar to relax and hustle a bit of pool while Sam stayed at the motel doing research like a total nerd, this is the type of situation that Dean currently finds himself in after a former fling notices him and proceeds to berate him for never calling her. Unfortunately, things have gone far beyond “awkward” and the option of charming his way into the woman’s bed again isn’t actually an option at all for the following reasons:

1) He’s currently fucking his brother. Exclusively. He would inform her of this, but common sense and the rules of propriety tell him that it’s probably not a great idea to announce that he engages in hardcore incestuous banging with his little brother on a regular basis.

And

2) She is _pissed_.

Like, holy freaking hell is she ever pissed; Dean is actually starting to feel mildly concerned for his personal safety. At first, he had been sure that he’d be able to talk his way out of the situation, except…

“You don’t even remember my _name_?”

Yeah. There’s that.

“Look,” Dean says placatingly, “it was a long time ago and my memory’s a bit fuzzy. And I’m pretty sure that it starts with an ‘R’ at least…Rachel, maybe?”

“My name is _Gertrude_ ,” she says icily.

“Wait, _seriously_?” he blurts out before backtracking and saying “I mean, of course it is. I knew that. Look Gertrude, we both had a great time together a few years back, but I never pretended that I wanted it to be a long-term thing.”

Her chin wobbles a little bit before she says, “I thought we had something special. Before you left in the morning, you said that we should do it again sometime-“

“-that’s an expression!”

“-and then you told me that you would call me. You lied to me.”

Dean sighs and feels a little bit of guilt well up inside of him. “Okay, look, I’m sorry if I gave you the impression that I wanted you to be my girlfriend and I’m really sorry if I hurt your feelings.”

Gertrude’s vulnerable expression suddenly turns steely as she declares “I don’t want your apologies. You used me, Dean Winchester. The only thing you were interested in was getting off and then making a clean break. But you know what I think? I think that you shouldn’t be able to get off at all unless you try being a little more honest with your partners.”

Dean wants to protest that he’s really not that kind of guy, but Gertrude leaves the bar in a flurry of anger before he can even get a word in. He thinks about sticking around and fulfilling his plan to hustle up some money and kick back with a few drinks, but the whole experience has left him a bit unsettled and not exactly in the mood. Instead, he heads back to the motel and decides to turn in early in the hopes that he’ll be able to forget about the whole thing by the time morning comes and he’ll be able to enjoy a nice, normal day (well, normal by Winchester standards anyway).

Predictably, that’s not quite what happens. Sure, things start off well enough; he wakes up to the sound of Sam click-clacking on his laptop and the feeling of his morning wood begging for attention. He manages to lure Sam away from his research for a little bit of morning sex and that’s where things start to get a bit dicey because a little bit of morning sex begins to turn into a _lot_ of morning sex that threatens to turn into afternoon sex because Dean _cannot freaking come_. It’s not that the sex isn’t good; hell, it’s great. There are few things in this world that Dean loves more than pressing his brother against the bed (or the wall. Or the shower. Or anything, honestly) and burying himself inside of his perfect ass. But the fact remains that Dean is hard as a rock, horny as all get-out, and can’t have an orgasm for anything (even though Sam has had plenty, the little bastard).

Right now, Sam has his mouth wrapped skillfully around his dick, taking Dean in so deeply that his nose is brushing up against Dean’s stomach; the sight alone is usually enough to set Dean off, but even though he feels like he’s right on the edge of coming, he just can’t and it’s really starting to piss him off. After a few more minutes, Sam take his mouth off of Dean’s dick with an obscene pop and takes a few seconds to rub his jaw and wipe off the saliva on his chin before speaking.

“Okay dude, what the hell? It’s been _hours_ and you still haven’t managed to come.”

“Oh really? I haven’t noticed,” Dean says sarcastically.

“Dean, having an erection for this long seriously isn’t healthy. Have you taken any, er, performance enhancing drugs or something?”

It’s possible that Dean has never been quite so offended in his entire life. “Are you asking me if I’m taking Viagra or some shit? Do you think I _need_ Viagra? I’m perfectly capable of getting erections all by myself, thanks.”

“I was just asking! There’s gotta be some reason for it…”

“Well, unless someone decided to slip some boner pills into my drink last night, I don’t think…” Dean trails off as he’s suddenly dawned with a horrible revelation, “oh shit.”

Sam begins to look even more concerned. “What, do you really think that someone drugged you last night? We might need to take you to the hospital or something.”

“No, but I think someone might have put a curse on me.”

“What the hell, Dean? You got maybe-cursed last night and didn’t think to tell me?,” Sam asks in frustration. 

“Hey, I didn’t even realize it until now! Freakin’ witches, man. I can’t believe that I didn’t see it before either. ‘Gertrude’ is so obviously a witch name; I mean, come on.”

Sam cocks his head in confusion and furrows his brow in a way that Dean would (secretly) consider adorable under normal circumstances but is too busy freaking out about being cursed with an ever-lasting hard-on to fully appreciate it.

“Dean, I’m going to need you to back way up. Who the hell is Gertrude and why would she curse you?”

“She’s this chick that I ran into at the bar last night. We had a, uh, _thing_ a while back-“

“-big surprise,” Sam snorts.

“-shut up. Anyway, she was ticked off that I never called her afterwards and said something about how I shouldn’t be able to get off unless I’m more truthful with the people I fuck…or something,” he explains.

Sam heaves out a sigh. “Great…so you managed to jilt a witch, and now you might die of magical priapism of all things. How the fuck do I explain that to people?”

“I didn’t mean to jilt her! It’s not like I promised to marry her for christ’s sake. I was just trying to sneak out of her house the next morning, got caught, and then let her give me her phone number so I could get the hell out of there. It was just meaningless sex; you know that I don’t like to get involved in all of that romance crap if I can help it. It just gets too messy.”

An expression of hurt flickers across Sam’s face at the end of Dean’s rant. “Right…meaningless sex. Is that what we do, Dean?,” he asks while turning his back to Dean.

Dean immediately feels like the biggest asshole in the world. “That isn’t…that’s not what I meant, Sammy. I just…”

“You just what? What _do_ you mean, Dean? If this is just meaningless, easy sex for you, then say it. Isn’t telling the truth the only way to break the curse anyway?”

Sam’s words hit him like a slap to the face. “Jesus Sam, how could you even think that?” he asks quietly.

Sam turns back around to look at Dean. “What am I supposed to think? We fuck all the time, but whenever I actually try to talk about our relationship, you change the subject. Sometimes I feel like,” he swallows before continuing, “…like maybe you’re just doing this out of opportunism. I mean, why put in the effort of picking up girls at a bar when you know that I’m an easy lay, right?”

Dean feels his throat tighten a little bit before he manages to say, “Sammy, you’re one of the smartest guys I know and that’s still one of the dumbest things I’ve ever heard. You’re not just some quick and easy fuck to me. You’re pretty much one of the only good things in my life, and you always have been. You gotta know that.”

Sam’s voice is so soft that Dean can barely make it out, but his unsure yet hopeful “Really?” breaks his heart a little bit.

“Of course you are! The only reason why I kept dodging you whenever you wanted to spill your heart out was because I knew that I would just fuck everything up. I know that I’m pretty good in the sack, but that’s all I’m good for,” he takes a deep, shaky inhale and continues before Sam can interject, “I figured that I’d just make a mess of things if we went any deeper than that and that I’d drive you off once you realized that you could do better and that would _wreck_ me, Sam. I couldn’t handle it if you left; I’d go off the deep end.”

Sam places his hand gently on Dean’s shoulder, and Dean can see that his eyes are wet. “Dean, you’re not going to drive me away, and you’re definitely good for a lot more than just sex. You’re the best thing in my life too, you know and I don’t want or need you to perform a bunch of grand romantic gestures or anything. And so what if you fuck things up every once in a while? I’m not expecting you to be perfect, Dean; we’re both allowed to screw up here,” he reaches over and laces his fingers with Dean’s before continuing, “the only important thing is that we’re able to be honest and up-front with each other so that we can work things out. That’s all I want.”

Dean doesn’t quite know what to say to that at first, so he cups Sam’s jaw and then pulls him into a deep, slow kiss while he gathers his words. “Yeah,” he says after they part, “I think I want that too.”

A little while later, as Dean is slowly and gently fucking Sam into the bed, he finally, finally comes inside of him and has never been so happy to see his dick flaccid in his entire life.

“Oh, thank God that’s over,” he groans.

“Gee,” Sam says dryly, “that’s just what every guy likes to hear after sex.”

“Oh, shut up. You know what I mean.”

After that, they fall into a comfortable silence before Sam asks, “You wanna know what’s kind of funny?”

“Is it the fact that we had a full-blown chick flick moment complete with a heart-to-heart talk a while ago while I had a comically large erection?”

“No! Well…yes, but I was going to so say that I think it’s a bit funny that the curse actually ended up doing some good for us. This is pretty much the only time that getting cursed by a witch has worked out for the better since, historically speaking, the Winchesters don’t exactly have a good track record with this kind of thing.”

“Oh yeah, Gertrude’s a real freakin’ saint,” Dean grumbles. “Maybe I’ll send her a cake that says ‘thanks for the death-boner’ on it.”

But later when Sam is fast asleep with his head on Dean’s chest, Dean thinks about how he feels lighter and happier than he has in years and wonders if maybe Gertrude does deserve a thank you after all.


	5. Curtain fic

**Summary for the Chapter:**

> Sam discovers that Dean has a very interesting hobby

Dean and Sam finally retired from hunting at the ripe old ages of 44 and 40 years old respectively after they both decided it was high time to say “fuck it” to the whole “saving the world” business (and the “maybe kind of putting the world in peril in the first place, oops” business that they occasionally engaged in for that matter). More and more hunters had been crawling out of the woodwork in the past several years and they both felt comfortable in letting the new generation hunt down monsters and assumed a more supportive role in hunting with Sam being content to be a full-time researcher and Dean taking responsibility for creating ID forgeries and impersonating federal officers.

For the first year of their retirement from hunting, Sam constantly felt like he was waiting for the other shoe to drop because he’d been kicked in the teeth by life enough times to know that “settling down” didn’t tend to work out well for the Winchester family. It seemed like there were always demons to stalk them, angels to drag them into apocalypses, and god knows what else conspiring to ruin their lives and Sam knew that Dean was probably just as edgy as he was. After a while though, it was surprisingly easy for them to adjust to a life filled with “all that domestic, white picket fence bullshit” (Dean’s words) and for the first time in years, they both found that they actually had time to pick up some hobbies.

Sam, for example, found himself becoming partial to gardening and Dean found himself becoming partial to mocking the crap out of Sam for said gardening until he promptly changed his tune and declared that gardening was quite possibly one of the best things on earth after seeing Sam garden shirtless under the hot sun while covered in dirt and glistening sweat on a regular basis.

One day when Sam was cruising through the bunker’s living room, he came across a word document displayed on Dean’s open laptop and discovered that Dean had a hobby of his own as well. Dean…well, Dean apparently liked to write fanfiction that catered to his obsession with _Dr. Sexy M.D._ (a tv show that, to Sam’s surprise, is still running after over 15 years. He does, however, reason that it’s probably a good thing that it’s still airing because he’s half-convinced that Dean would track down a crossroads demon if it ever actually got cancelled). After reading through the fanfiction (which was titled ‘Pleasuring the Patient;’ nice, Dean) Sam found it to not only be every bit as raunchy as the title implied, but it almost seemed as if the patient in question who banged Dr. Sexy in supply closets, on operating tables, and, in one case, a coma patient’s room (what the fuck, Dean) was written as being suspiciously similar to Dean himself. Exactly similar in fact, right down to the green eyes and bowed legs.

Sam was so busy deciding whether or not he should take the high road and forgo teasing Dean for the rest of his life that he failed to hear the front door of the bunker open and was still scrolling through a very graphic sex scene involving creative usage of medical stirrups when Dean suddenly dived towards the laptop and slammed it shut.

Dean’s face was bright red and his voice was slightly screechy as he asked “What the hell are you doing, Sam?! You can’t just use another man’s laptop without asking!”

Sam crossed his arms and adopted an extremely unimpressed expression. “Really, Dean? You’ve stolen my laptop a million times over the years so that you could jerk off to porn and give me computer viruses and you’re lecturing me about computer privacy?” Seeing as Dean appeared unable to come up with a suitable retort to that point at the moment, Sam smirked and continued, “besides, I was just reading an extremely riveting story about a rugged fireman who’s taken to the hospital after being injured while rescuing children from a burning building and somehow manages to get fucked back to good health by Dr. Sexy. I’m just trying to be supportive of your creative writing endeavors, big brother.”

“What, you think I wrote that? You know there’s no way I would be caught dead doing something as dorky as writing _fanfiction_. I was just…holding it for a friend,” Dean finished lamely. “…shit, that doesn’t make sense. Okay fine, I wrote it. There.” He crossed his arms and looked at Sam challengingly. “If you’re gonna make fun of me then just go ahead and do it. Get it all out.”

Sam rolled his eyes at Dean’s dramatics. “Jeeze, I wasn’t gonna make fun of you, Dean. Well, I mean, I was but this is entertaining enough. How the hell did you even start writing fanfiction anyway?”

Dean’s defiant look turned slightly sheepish before saying, “You know how the fans of that goddamn book series like to write about us banging and confessing our undying love for each other? I figured that if people wrote that kind of crap about us, then they probably did it for other things too and it turns out that there’s like a million _Dr. Sexy_ fanfics out there. Except most of them have Dr. Sexy hooking up with Elizabeth, the head orthopedic surgeon, which doesn’t even make _sense_ because she totally sabotaged his chances of a promotion in season four and they’ve hated each other ever since. I figured that it was my duty to write about Dr. Sexy getting it on with a _good_ character.”

“Riiiight,” Sam drawled, “And you figured that the character should be yourself?”

“Whoa, that isn’t me!” Dean shouted, affronted.

“Are you seriously trying to tell me that Don Barrett isn’t supposed to be a thinly veiled version of yourself?”

“Well,” Dean admitted, “I might have _inspired_ him, but just because he’s devastatingly handsome and irresistibly charming doesn’t mean-“

“-and are you also going to tell me that that the malpractice lawyer that Don and Dr. Sexy have a threesome with during chapter four in the on-call room isn’t meant to be me?,” Sam interrupts with a raised eyebrow.

Dean tries to look flummoxed. “Why the hell would you think that?”

“Well, his name is _Cam_ and he’s described as being ‘tall as fuck’ and possessing ‘an ass so perfectly sculpted that it could make an angel weep like a little bitch.’”

“Gee Sam, you’re being awfully vain right now…”

“You also literally call him ‘Sam’ in the eighth paragraph,” he points out.

“Shit, seriously? I need a freakin’ beta,” Dean mutters. “Alright, so maybe I wrote about us having a threesome with Dr. Sexy. Can you blame me? It’s pretty much my ultimate fantasy; I’m at half-mast just thinking about it.”

Sam leaned over and ran his hand down Dean’s thigh. “Well,” he says lowly, “I can’t exactly promise you a threesome with Dr. Sexy due to the fact that he’s, you know, not real and all, but I _can_ help you re-enact some of the other scenes you wrote about if you want.”

And, hell, it’s not like Dean could turn an opportunity like that down. Maybe he would even get some inspiration for his next chapter…


	6. Undercover

**Summary for the Chapter:**

> Sam goes undercover as a priest and Dean is into it. _Really_ into it.

**Notes for the Chapter:**

> I would probably place this early on in the series, but it doesn't really matter (I guess it would technically have to placed before season 10 though because Dean has a line where he mentions never having gone to confession and this isn't true after that season)

Sam figured that it probably said something about his life that this wasn’t the first time that he’d impersonated a Catholic priest, but after several members of a small town Californian parish began dying in increasingly bizarre ways, it seemed like the most logical choice. Still though, he almost envied Dean for getting to take a custodial position in the church while he was stuck with the role of a newly transferred priest (which the church desperately needed since the other ones kept, well, _dying_ and everything). Earlier, he had been stuck in a confessional booth for over an hour listening to people give him their confessions, and while he encountered numerous interesting parishioners (including an elderly woman who first confessed to selling store-bought cookies in a bake sale and then immediately proceeded to admit that she had also recently engaged in an extramarital threesome with her aerobics instructor and her grandson’s piano teacher), he hadn’t heard anything that remotely helped him with the case. He was also starting to feel a bit guilty for accepting confessions in the first place since he couldn’t exactly offer anyone genuine absolution due to the fact that he wasn’t technically a priest at all.

The church was long empty now and Sam had decided to use the seclusion and privacy of one of the confessional booths to once again review what little information he and Dean had about the case. He was in the middle of wondering where the hell Dean was and whether he had found anything substantial when he heard the sound of the booth’s other door creak open so that someone could step inside. Sam cleared his throat and was just about tell them that confessional hours were over when he heard the unmistakable husky voice of his brother.

“Bless me father, for I have sinned. My last confession was, uh, never ago…”

While Dean paused, Sam debated telling him to knock it off so that they could discuss the case, but instead decided to play along because he was curious as to where Dean was going with it: “Please continue, my son. What are your sins?”

Dean let out a laugh and Sam could practically see the smirk on his face. “We’ll be here all day if I have to list them all, but right now the main one is probably the fact that I’m doing my brother.”

Sam was getting the distinct feeling that Dean’s confession was about to become a lot more X-rated, but a part of him was starting to really get into the spontaneous roleplaying that Dean decided to spring on him. “As I’m sure you’re aware, incest is a mortal sin; how many times have you engaged in…relations with your brother?,” Sam asked.

“Oh, we’ve definitely been sinning on a regular basis. To be completely honest with you, Father, my brother is a bit of a slut. He practically begs for my dick pretty much every single day, and I’m sure as hell not a strong enough man to deny him,” Dean said.

Sam thought that _begging_ for it was a little bit of an exaggeration, but he couldn’t deny that the whole thing was beginning to turn him on. “And why do you think that you’re compelled to do such things with your brother? Is sexual pleasure truly worth endangering your mortal soul?”

“What about him _doesn’t_ compel me? He has this tight, perky little ass that looks even more amazing when it’s being stretched open around my dick and he makes the neediest sounds whenever I fuck him. He’s pretty loud when he does it too; sometimes I think the whole motel can hear him begging me to fuck him harder,” Dean took a second to pause before continuing and Sam felt himself lean forward in anticipation, “Usually, he loves it when I pin him to the bed and give it to him good and hard, but sometimes he likes to push me down so that he can climb on top of me and ride me like he’s getting paid for it. God, the way he bounces up and down on my dick has got to be one of the best sights in the world. It’s almost as good as the way he looks after we’re finished, with his hair all messed up, his face flushed, and his legs spread wide enough that I can see my come leak down his thighs. Is that answer enough for you, Father?”

Sam had been fostering a hard-on since mid-way through Dean’s speech and his voice was slightly strangled as he said, “Surely, that’s not all you’ve done with your brother? Perhaps I need to hear more in order to determine your penance.”

“I don’t know, Father,” Dean drawled, “I’ve been doing an awful lot of talking. Maybe I’ll just _show_ you instead and work off some of that penance right here”

Sam couldn’t even get in a reply before he heard the Dean open the door to exit his side of the booth and then came into his own and pinned him against the wall with a rough kiss.

“Wow, you’re pretty sexy for a priest, aren’t you? If I had known they made them like you in seminary school, I might have gone into a different line of work,” he said when he pulled away.

Sam grinded his erection into Dean’s thigh and let out an impatient moan. “I thought you said you were done talking? I’m a lot more interested in finally getting that dick of yours inside me.”

“Sheesh, and you talk dirty for one too. A little patience goes a long way, Father.” But despite his words, Sam could tell that Dean was just as eager as him as he was already fumbling with the zipper of his pants and taking out his dick with one hand while using the other to lift up the hem of Sam’s cassock so that he could palm Sam’s bare ass.”

He let out a low whistle. “Don’t most priests wear pants under these things? Not to mention underwear. Isn’t it a sin to go commando in the house of the Lord or something?”

Sam happened to enjoy the breezy feeling that the cassock gave him, but decided to forgo explaining that in favor of turning away from Dean and bracing himself on the confessional’s bench. “I’m waiting.”

“Alright, alright,” Dean muttered, “no need to be pushy.”

Sam could hear the sound of a foil packet of lube being torn open and wondered how long Dean had been waiting to do this if he had the foresight to bring lube to church, but all of his thoughts flew out of his head as soon as he felt Dean circle his rim briefly with two slick fingers before shoving them inside of him with little preamble.

“Shit, you’re so fucking tight,” he groaned as Sam gasped and rocked desperately against his fingers.

Normally, Dean liked to tease Sam and work his fingers inside of him for what always felt like an eternity before fucking him, but he was so worked up that it was no time at all before he was guiding his dick to Sam’s hole and thrusting in until his balls rested against Sam’s ass.

Sam’s grip on the bench tightened and Dean’s hands glided up and down his back soothingly while he got used to the stretch. “Oh my God,” Sam groaned, “just move.”

“Hey now, no taking the Lord’s name in vain,” Dean said before giving Sam’s ass a light smack as he obliged his request and began setting a steady in-and-out pace. “If you keep this up, _you’ll_ be the one confessing your sins next.”

It wasn’t long before Dean’s thrusting grew more frantic and he was pounding into him so hard that Sam could feel the confessional booth shaking. One of Dean’s hands was leisurely jerking Sam off while the other one was yanking back on the stiff collar in his cassock until Sam was arching his back so far that he was practically flush with Dean’s chest.

“Oh Father,” Dean whispered into his ear, “is this enough penance for you?”

Sam tensed and came with a strangled cry and it wasn’t long afterwards that he felt Dean’s pace become unsteady and jerky before he moaned into Sam’s ear and spilled inside of him.

For a few minutes afterwards, they both remained quiet as they enjoyed the afterglow and Dean placed soft, lazy kisses on the back of Sam’s sweaty neck. “God,” he said, “I’ve been wanting to do that ever since I first saw you wearing this dress thing.”

Sam rolled his eyes and slapped Dean’s chest lightly. “It’s a _cassock_. I know that you know that.”

“Well whatever it is, it’s got come all over it so I hope you have a back-up.”

“The sheer amount of blasphemy in that statement and in everything else we’ve done during the past hour is staggering,” Sam said.

“If it makes you feel better, it was probably the sexiest blaspheming I’ve ever done,” Dean said with a leer.

“Yeah, it was.” Sam admitted. After a few seconds of silence, he asked, “Are you sorry?”

“Huh?”

“When you were confessing, we never actually got to the part where you really apologized for your sins and gave an Act of Contrition. Are you ready to apologize and resolve to give up your sinful, brother-fucking ways?”

Dean snorted. “Hell no, Sammy. We’re just barely getting started; I plan to spend the rest of my life sinning with you.”

Sam smiled and drew Dean into a slow, gentle kiss.

“Amen.”


	7. Valentine's Day

**Summary for the Chapter:**

> Dean fondly remembers being Sam's first Valentine

Dean was Sam’s very first Valentine; it’s been more than twenty-five years, but Dean can still clearly remember his chubby, floppy haired brother running up to him after school with glitter covering his shirt and an equally glittery Valentine’s Day card clutched in his fist. At first, Dean thought that Sam was sweet on one of the girls in his first grade class, but with a toothy grin, Sam informed him that his teacher told the class that they should make Valentines for someone who was special to them and then write why they loved that person inside of the card.

“And you’re the person that I love the most,” Sam concluded earnestly as Dean felt a surge of adoration for his brother and examined the Valentine that Sam shoved at him eagerly.

Inside of the card, Sam’s childish scrawl declared:

“Dean,

I love you because you can cook mac and cheese and you let me be Batman sometimes when we play even though he’s your favorite. You are the best big brother ever.

Love, Sam.”

Underneath his words were two stick figures holding hands that Dean presumed were meant to be he and his brother. The card itself was a garish looking heart-shaped thing covered in lace and stickers and managed to get an astonishing amount of glitter on whatever poor soul handled it, but to Dean it was a masterpiece. Even at tender age of 11, Dean was a burgeoning ladies’ man and had no shortage of Valentines given to him by hopeful girls over the past couple of years but while he enjoyed the attention, Sam’s was still the most significant to him. Dean didn’t have a card for Sam, but he shared his mountain of chocolate and cookies (courtesy of the girls in his class) with him and later that night, they both gorged until they felt sick and fell asleep in a tangle of limbs in front of their motel room’s crappy television.

Sam didn’t know it until decades later, but Dean kept that glittery monstrosity tucked into his wallet for years so that he could take it out every so often and re-read the words that he had long memorized. These occasions only increased in frequency after Sam went to Stanford, and when Dean was feeling especially maudlin, he would get drunk and take out the card and wallow in nostalgia about the days when Sam worshipped the ground he walked on and stuck to him like glue. At that point, the card’s red construction paper was faded, worn and creased, most of the stickers had peeled off, and even the generous amount of glitter that originally plagued it had all but fallen off completely, but Dean still regarded it as a precious treasure for its sentimental value and the fact that it was one of the only tokens of Sam that he had left.

A couple of years after Sam left, Dean lost his wallet in a werewolf-hunt gone wrong, and while having to replace all of his fake credit cards and IDs had been a pain in the ass, it was the loss of the card more than anything else that felt like a knife to the heart.

One February day in the bunker while they were both tipsy and somehow got on the topic of discussing their best and worst Valentine’s Day experiences, Dean confessed to hanging on to the card that Sam gave him so long ago and to choking up when he lost it years later. He expected Sam to tease him about it, but instead his brother’s gaze just grew a little softer and contemplative as he tangled his fingers with Dean’s.

The combination of tequila and the mind-blowing sex that he and Sam had afterwards caused Dean to nearly forget about the whole thing until he woke up a few days later on February 14th to find a heart- shaped card on his nightstand. This one was admittedly more tasteful than the enthusiastic efforts of seven year old Sam as the card lacked an abundance of lace and stickers (although Dean soon found out that the little bastard still filled the inside of it with glitter just to mess him). When Dean opened the card, he found a handwritten message from Sam:

“Dean,

I love you because I know that, even though we’ve literally been through hell for each other, you’ll always be there for me no matter what kind of crazy apocalyptic doomsday we’re trying to prevent at any given time. Our lives may be filled with monsters and general insanity, but I’m glad that we get to spend the rest of them with each other. You’re my best friend, soul-mate, and remain the best big brother ever.

Love, Sam.

P.S. You still make great mac and cheese.”

With a lump in his throat, Dean traced the words with his fingers for a few minutes before gently folding the card and giving it a rightful spot in his wallet.

Sam may not have been _Dean’s_ first Valentine, but Dean hoped to God (wherever that asshole may be) that he would be his last.


End file.
